A large number of naturally occurring quinones can be classified as potential bioreductive alkylating agents. Such compounds are proposed to undergo an in vivo reduction to the corresponding hydroquinone, and this reduced form can function as a potent alkylating agent. Among such bioreductive alkylating agents are the mitomycins, kinamycin, nanaomycin, and adriamycin. The objectives of this proposal are to develop synthetic routes to these natural products and their analogs. It is most desirable to develop synthetic methodology which can be used not only for the construction of the natural products but also for those analogs which have the structural features believed to be necessary for biological acitivity. At the present time, the primary synthetic effort is directed towards mitomycin C and closely related analogs.